Sometimes, to comply with the regulations requires a crew with you. I believe the regulations describe your situation and say that somebody in contact with the pilot is briefed on the mission and someone must have their eyes on the drone at all times.
Flying on the other side of a big water tower or forest is a good way to get into a radio shadow and lose the drone.
A very competent commercial drone pilot showed up to map the creek and wetlands at a buddy's waterfront property in preparation for dredging, seawall, and dock projects over about 100 acres. He stationed crew where they could keep their eyes on the drone and conference-called with the crew so they could chatter. He lost the signal on his first attempt, the drone did RTH, and he re-positioned himself on another dock and finished the job. It could have been worse and one of his spotters could be running after a drone.
I could have done the whole job, entirely illegally, with DroneDeploy and charged a few dollars for it like some jacklegs would do. He did it entirely legally, paid a crew, did a beautiful job, and got a thousand bucks.
When we get Remote Id you can pay into the system, buy compliant drones, plan your flight with Litchi or other app, and let your drone loose to fly it. Meanwhile it's VLOS rules...